


Enjoy And Don't Hold Back

by SinQueen69



Series: Requests [84]
Category: Teen Wolf (TV)
Genre: Age Difference, Anal Fingering, Blow Job, Collar, Come Swallowing, Coming Untouched, Don't copy to another site, Light Bondage, M/M, Multiple Orgasms, Oral Fixation, Oral Sex, Passing Out, Prompt Fill, Virgin Stiles Stilinski, bullet vibe, leather cuffs, sex toy
Language: English
Status: Completed
Published: 2020-09-08
Updated: 2020-09-08
Packaged: 2021-03-06 15:26:54
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 881
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26361124
Author URL: https://archiveofourown.org/users/SinQueen69/pseuds/SinQueen69
Summary: Request Anon's Wanted:Derek and Stiles have been in a relationship for a while and they haven’t had sex. So one night Derek suggests that they have sex and Stiles confesses that he is a virgin. Derek finds that hot and says he doesn’t care, so when they start to do it Derek realizes that Stiles’s sensitive spot is in his mouth. So Derek gets the idea to have Stiles suck on lollipops while he jacks off, and Stiles cums a lot. Once Stiles has so much pleasure that he would do anything Derek tells Stiles to suck his dick off. Stiles does it, Derek comes in Stiles’s mouth and Stiles passes out from the amount of cum.+Can you write some light bondage Sterek with Stiles (or maybe Derek either one is cool) with an ohmibod device in him and the other is controlling it. Usually they’re used by camgirls and it’s powered by viewer donations but I think it goes against your No New Chapter rule so it doesn’t have to be cam!Stiles or anything similar to what you’ve written before. I just like the idea of Stiles having a strong vibrator and Derek in control of it.
Relationships: Derek Hale/Stiles Stilinski
Series: Requests [84]
Series URL: https://archiveofourown.org/series/1618726
Comments: 3
Kudos: 264





	Enjoy And Don't Hold Back

“Are the collar and cuffs really needed?” Stiles asked around the cherry lollipop in his mouth, his fingers curling just below his chin. 

The thick collar Derek had wrapped around his boyfriend’s throat had a ring at the front that Derek hooked the short chains from Stiles’ wrist cuffs too. Stiles couldn’t move his arms and his fingers could only reach his mouth to move the lollipop but Stiles did as he was told and kept sucking at the candy, Derek insisting he kept something in his mouth at all times. 

“Yes, trust me, baby,” Derek crooned at his cute, virgin boyfriend as he lazily stroked Stiles’ erection, teasing the wet head and smooth balls as he lay on the bed next to Stiles, dark eyes sweeping over the younger man’s trembling naked body.

When Stiles had admitted that he was a virgin when they got to that stage in dating, Derek had promised him that it didn’t matter to him, that they would go slow. What Derek didn’t tell him was that Derek was incredibly turned on by the fact Stiles’ was a virgin, this way every new sensation was given to Stiles by Derek and would always pair those sensations to Derek. It was a heady feeling and Derek pressed his thumb against the underside of Stiles’ cock head, loving the whine and wiggle Stiles made at the pressure. 

Derek removed his sticky hand from his boyfriend’s cock and applied lube to his fingers before curving his hand between Stiles’ thighs, rubbing at his boyfriend’s tight, virgin hole.

“Don’t worry Stiles,” Derek shushed the wide-eyed boy who squirmed and started to say his name. 

“Just one finger and then something special that I got just for you.” Derek crooned as he pressed his index finger against Stiles’ hole and watched Stiles’ cock jerk and spurt cum as he eased his finger into his boyfriend’s tight ass. 

“Feels good right?” Derek nuzzled Stiles’ cheek, loving the flush look on Stiles’ face and the way he was sucking at the lollipop like his life depended on it. 

“Y-Yeah didn’t expect that,” Stiles admitted a bit breathless. Derek massaged Stiles’ inner walls a bit with his finger, just coaxing the virgin tight hole open enough for what he had planned next. Derek smiled at the sight of Stiles’ cock already hardening. Stiles made a disappointed noise when Derek slipped his finger out of him making Derek chuckle. 

“This will make up for it, don’t worry,” Derek promised as he wet a small bullet vibrator, a cord hanging from the end so he could tug it out after. Stiles sucked harder and louder at the sight of the small vibe but shifted his legs wider in silent permission. 

Derek smiled as he moved his hand back down to Stiles’ hole and nudged the vibe in, Derek resisted smirking when Stiles hole just swallowed it with only a little of pressure from him. Stiles gasped around the lollipop, fingers catching it before it fell completely from his mouth. 

“Enjoy yourself Stiles and don’t hold back.” Derek kissed Stiles’ cheek before he hit a small button on a remote that he had hidden from Stiles’ view. 

Stiles cried out, body arching off the bed as he came again when the vibe turned on. The buzzing was so intense it had Stiles’ hips shaking and his cock rapidly filling even before his fresh release had cooled on his stomach. 

Derek played with the intensity of the vibrations; drawing orgasm after orgasm from his virgin boyfriend until Stiles was sobbing around the lollipop he was still dutifully sucking. 

“Derek, Derek, please, I can’t anymore, please, my cock hurts.” Stiles’ eyes were glassy with unshed tears and Derek wiped a stray one away as Stiles’ cock jerked weakly and small dribbles of cum came from the wet slit. 

“I’ll turn off the vibe if you be a good boy and let me use that pretty mouth to get off,” Derek suggested as he traced Stiles’ sticky, red lips. 

“Yes, yes, anything!” Stiles nodded, taking the worn down lollipop stick from his lips and opened his mouth wide for him to use. 

“That’s a good boy,” Derek straddled Stiles’ face as he turned the vibe off. Derek cut off Stiles' noise of relief by pushing his cock into the younger man’s mouth. Derek moaned and grabbed onto the wall behind the bed as he rolled his hips, lazily fucking his boyfriend’s mouth. Stiles’ drooled around the older man’s large cock, unused to having something so big filling his mouth. Derek didn’t mind the sloppiness; all he cared about was reaching his orgasm. 

Derek moaned and ground his cock deep in Stiles’ throat, balls resting on Stiles’ chin as he did so. Derek grabbed Stiles’ hair to keep him in place he cried out, filling Stiles’ mouth with his cum. Derek looked down just in time to see Stiles’ eyes roll up into his head and his mouth went slack around Derek’s cock as he passed out.

Derek quickly pulled out of Stiles’ mouth and watched as Stiles swallowed even in his unconscious state. Derek felt smug as he took in the debauched state his virgin boyfriend was in thanks to him and Derek hadn’t even properly fucked him yet.


End file.
